ES2389271T3 - Amidas novedosas que actúan sobre los receptores de adenosina - Google Patents
Amidas novedosas que actúan sobre los receptores de adenosina Download PDFInfo
- Publication number
- ES2389271T3 ES2389271T3 ES07846549T ES07846549T ES2389271T3 ES 2389271 T3 ES2389271 T3 ES 2389271T3 ES 07846549 T ES07846549 T ES 07846549T ES 07846549 T ES07846549 T ES 07846549T ES 2389271 T3 ES2389271 T3 ES 2389271T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- ethyl
- propionamide
- phenyl
- indole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001408 amides Chemical class 0.000 title claims abstract description 12
- 108050000203 Adenosine receptors Proteins 0.000 title description 14
- 102000009346 Adenosine receptors Human genes 0.000 title description 14
- -1 sulfonic Chemical group 0.000 claims abstract description 101
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 125000004385 trihaloalkyl group Chemical group 0.000 claims abstract description 9
- 125000004952 trihaloalkoxy group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 4
- 125000002015 acyclic group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 229940080818 propionamide Drugs 0.000 claims description 58
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 6
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- NLMQYWMOPYXYMS-UHFFFAOYSA-N n-[1-(2-chloro-4-fluorophenyl)-2-(4-fluoroanilino)-2-oxoethyl]-3-(diaminomethylideneamino)-n-[2-(5-methoxy-1h-indol-3-yl)ethyl]propanamide Chemical compound C12=CC(OC)=CC=C2NC=C1CCN(C(=O)CCN=C(N)N)C(C=1C(=CC(F)=CC=1)Cl)C(=O)NC1=CC=C(F)C=C1 NLMQYWMOPYXYMS-UHFFFAOYSA-N 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- CTBWWPIIRKWDDL-UHFFFAOYSA-N 3-amino-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(N)=C1 CTBWWPIIRKWDDL-UHFFFAOYSA-N 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- NTVAXZHNGVSFIR-UHFFFAOYSA-N 3-(diaminomethylideneamino)-n-[2-(4-fluoroanilino)-2-oxo-1-[4-(trifluoromethyl)phenyl]ethyl]-n-[2-(6-fluoro-1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC(F)=CC=C2C=1CCN(C(=O)CCN=C(N)N)C(C=1C=CC(=CC=1)C(F)(F)F)C(=O)NC1=CC=C(F)C=C1 NTVAXZHNGVSFIR-UHFFFAOYSA-N 0.000 claims description 2
- CCZKXFFULPFMPX-UHFFFAOYSA-N 3-amino-n-[1-(2-bromophenyl)-2-(4-fluoroanilino)-2-oxoethyl]-n-[2-(1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(C(=O)CCN)C(C=1C(=CC=CC=1)Br)C(=O)NC1=CC=C(F)C=C1 CCZKXFFULPFMPX-UHFFFAOYSA-N 0.000 claims description 2
- JSHDYVFUFJNPEP-UHFFFAOYSA-N 3-amino-n-[1-(2-chloro-4-fluorophenyl)-2-(4-fluoroanilino)-2-oxoethyl]-n-[2-(5-methoxy-1h-indol-3-yl)ethyl]propanamide Chemical compound C12=CC(OC)=CC=C2NC=C1CCN(C(=O)CCN)C(C=1C(=CC(F)=CC=1)Cl)C(=O)NC1=CC=C(F)C=C1 JSHDYVFUFJNPEP-UHFFFAOYSA-N 0.000 claims description 2
- RYAOPQHUMCNUGK-UHFFFAOYSA-N 3-amino-n-[2-(4-fluoroanilino)-2-oxo-1-[4-(trifluoromethyl)phenyl]ethyl]-n-[2-(5-methoxy-1h-indol-3-yl)ethyl]propanamide Chemical compound C12=CC(OC)=CC=C2NC=C1CCN(C(=O)CCN)C(C=1C=CC(=CC=1)C(F)(F)F)C(=O)NC1=CC=C(F)C=C1 RYAOPQHUMCNUGK-UHFFFAOYSA-N 0.000 claims description 2
- PUFCIPQDDLDNKA-UHFFFAOYSA-N 3-amino-n-[2-(4-fluoroanilino)-2-oxo-1-[4-(trifluoromethyl)phenyl]ethyl]-n-[2-(6-fluoro-1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC(F)=CC=C2C=1CCN(C(=O)CCN)C(C=1C=CC(=CC=1)C(F)(F)F)C(=O)NC1=CC=C(F)C=C1 PUFCIPQDDLDNKA-UHFFFAOYSA-N 0.000 claims description 2
- HEASLFRZYVEIII-UHFFFAOYSA-N 3-amino-n-[2-anilino-1-(4-chloro-3-nitrophenyl)-2-oxoethyl]-n-[2-(6-fluoro-1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC(F)=CC=C2C=1CCN(C(=O)CCN)C(C=1C=C(C(Cl)=CC=1)[N+]([O-])=O)C(=O)NC1=CC=CC=C1 HEASLFRZYVEIII-UHFFFAOYSA-N 0.000 claims description 2
- JCQRNCDABZOFFV-UHFFFAOYSA-N 4-(1h-indol-3-yl)-2-methylbutanamide Chemical compound C1=CC=C2C(CCC(C)C(N)=O)=CNC2=C1 JCQRNCDABZOFFV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- RGJSQQOYFHTIAF-UHFFFAOYSA-N n-[1-(2-bromophenyl)-2-(4-fluoroanilino)-2-oxoethyl]-3-(diaminomethylideneamino)-n-[2-(1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(C(=O)CCN=C(N)N)C(C=1C(=CC=CC=1)Br)C(=O)NC1=CC=C(F)C=C1 RGJSQQOYFHTIAF-UHFFFAOYSA-N 0.000 claims description 2
- CZGCAEYEMWLNTC-UHFFFAOYSA-N n-[1-(2-chloro-4-fluorophenyl)-2-(4-fluoroanilino)-2-oxoethyl]-3-(diaminomethylideneamino)-n-[2-(6-fluoro-1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC(F)=CC=C2C=1CCN(C(=O)CCN=C(N)N)C(C=1C(=CC(F)=CC=1)Cl)C(=O)NC1=CC=C(F)C=C1 CZGCAEYEMWLNTC-UHFFFAOYSA-N 0.000 claims description 2
- JVYUGOGTXDTKTB-UHFFFAOYSA-N n-[2-anilino-1-(2-bromophenyl)-2-oxoethyl]-3-(diaminomethylideneamino)-n-[2-(1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(C(=O)CCN=C(N)N)C(C=1C(=CC=CC=1)Br)C(=O)NC1=CC=CC=C1 JVYUGOGTXDTKTB-UHFFFAOYSA-N 0.000 claims description 2
- YSUINKOAYPQIEV-UHFFFAOYSA-N n-[2-anilino-1-(2-chlorophenyl)-2-oxoethyl]-3-(diaminomethylideneamino)-n-[2-(1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(C(=O)CCN=C(N)N)C(C=1C(=CC=CC=1)Cl)C(=O)NC1=CC=CC=C1 YSUINKOAYPQIEV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000002917 arthritic effect Effects 0.000 claims 2
- ASEIJVVERNUQEB-UHFFFAOYSA-N n-[2-anilino-1-(4-methoxy-2,5-dimethylphenyl)-2-oxoethyl]-3-(diaminomethylideneamino)-n-[2-(1h-indol-3-yl)ethyl]propanamide Chemical compound C1=C(C)C(OC)=CC(C)=C1C(C(=O)NC=1C=CC=CC=1)N(C(=O)CCN=C(N)N)CCC1=CNC2=CC=CC=C12 ASEIJVVERNUQEB-UHFFFAOYSA-N 0.000 claims 2
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- LROPKPFFHCOGIY-UHFFFAOYSA-N 3-amino-n-[2-(4-chloroanilino)-1-(4-chlorophenyl)-2-oxoethyl]-n-[2-(1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(C(=O)CCN)C(C=1C=CC(Cl)=CC=1)C(=O)NC1=CC=C(Cl)C=C1 LROPKPFFHCOGIY-UHFFFAOYSA-N 0.000 claims 1
- IUNVSVRDVOYOMJ-UHFFFAOYSA-N 3-amino-n-[2-anilino-1-(2-chloro-4-fluorophenyl)-2-oxoethyl]-n-[2-(1h-indol-3-yl)ethyl]propanamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(C(=O)CCN)C(C=1C(=CC(F)=CC=1)Cl)C(=O)NC1=CC=CC=C1 IUNVSVRDVOYOMJ-UHFFFAOYSA-N 0.000 claims 1
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- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 210000005222 synovial tissue Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008718 systemic inflammatory response Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000007838 tissue remodeling Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0622826 | 2006-11-15 | ||
| GBGB0622826.6A GB0622826D0 (en) | 2006-11-15 | 2006-11-15 | Novel amides acting on the adenosine receptors |
| PCT/EP2007/009721 WO2008058679A2 (en) | 2006-11-15 | 2007-11-09 | Novel amides acting on the adenosine receptors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2389271T3 true ES2389271T3 (es) | 2012-10-24 |
Family
ID=37605369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07846549T Active ES2389271T3 (es) | 2006-11-15 | 2007-11-09 | Amidas novedosas que actúan sobre los receptores de adenosina |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8227502B2 (de) |
| EP (1) | EP2099815B1 (de) |
| JP (1) | JP5536456B2 (de) |
| KR (1) | KR20090091166A (de) |
| AU (1) | AU2007321460B2 (de) |
| CA (1) | CA2669162C (de) |
| ES (1) | ES2389271T3 (de) |
| GB (1) | GB0622826D0 (de) |
| IL (1) | IL198618A (de) |
| MX (1) | MX2009005023A (de) |
| NZ (1) | NZ576781A (de) |
| WO (1) | WO2008058679A2 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0019357D0 (en) * | 2000-08-07 | 2000-09-27 | Melacure Therapeutics Ab | Novel phenyl guanidines |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5007067A (en) | 1989-09-29 | 1991-04-09 | At&T Bell Laboratories | Diversity coding for transparent self-healing communications networks |
| DE10110747A1 (de) * | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte 2,6-Diamino-3,5-dicyano-4-aryl-pyridine und ihre Verwendung |
| RU2334742C2 (ru) * | 2003-01-13 | 2008-09-27 | Ф.Хоффманн-Ля Рош Аг | Производные бензоксазола и фармацевтическая композиция, обладающая свойствами лигандов рецептора аденозина |
| SI1633355T1 (sl) * | 2003-05-30 | 2008-08-31 | Hoffmann La Roche | Derivati benzotiazola in njihova uporaba pri zdravljenju bolezni, povezanih z receptorjem a2a adenozina |
| US7217702B2 (en) * | 2004-04-02 | 2007-05-15 | Adenosine Therapeutics, Llc | Selective antagonists of A2A adenosine receptors |
| EP1778712B1 (de) * | 2004-08-02 | 2013-01-30 | University Of Virginia Patent Foundation | 2-propynyl-adenosin-analoga mit modifizierten 5'-ribosegruppen mit a2a-agonistenaktivität |
| US7576069B2 (en) | 2004-08-02 | 2009-08-18 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
| WO2006091896A2 (en) | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Pyridyl substituted xanthines |
| US7579348B2 (en) | 2005-02-25 | 2009-08-25 | Pgxhealth, Llc | Derivatives of 8-substituted xanthines |
| US7598379B2 (en) * | 2005-02-25 | 2009-10-06 | Pgx Health, Llc | Methods for the synthesis of unsymmetrical cycloalkyl substituted xanthines |
| WO2006091898A2 (en) | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Pyrazolyl substituted xanthines |
-
2006
- 2006-11-15 GB GBGB0622826.6A patent/GB0622826D0/en not_active Ceased
-
2007
- 2007-11-09 EP EP07846549A patent/EP2099815B1/de not_active Not-in-force
- 2007-11-09 JP JP2009536639A patent/JP5536456B2/ja not_active Expired - Fee Related
- 2007-11-09 KR KR1020097012201A patent/KR20090091166A/ko not_active Application Discontinuation
- 2007-11-09 WO PCT/EP2007/009721 patent/WO2008058679A2/en active Application Filing
- 2007-11-09 ES ES07846549T patent/ES2389271T3/es active Active
- 2007-11-09 US US12/514,634 patent/US8227502B2/en not_active Expired - Fee Related
- 2007-11-09 NZ NZ576781A patent/NZ576781A/en unknown
- 2007-11-09 AU AU2007321460A patent/AU2007321460B2/en not_active Ceased
- 2007-11-09 CA CA2669162A patent/CA2669162C/en not_active Expired - Fee Related
- 2007-11-09 MX MX2009005023A patent/MX2009005023A/es active IP Right Grant
-
2009
- 2009-05-07 IL IL198618A patent/IL198618A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2669162C (en) | 2015-02-10 |
| JP5536456B2 (ja) | 2014-07-02 |
| JP2010509383A (ja) | 2010-03-25 |
| EP2099815B1 (de) | 2012-06-20 |
| IL198618A0 (en) | 2010-02-17 |
| WO2008058679A2 (en) | 2008-05-22 |
| MX2009005023A (es) | 2009-05-20 |
| US20100098629A1 (en) | 2010-04-22 |
| EP2099815A2 (de) | 2009-09-16 |
| GB0622826D0 (en) | 2006-12-27 |
| IL198618A (en) | 2013-07-31 |
| AU2007321460A1 (en) | 2008-05-22 |
| CA2669162A1 (en) | 2008-05-22 |
| AU2007321460B2 (en) | 2012-05-03 |
| US8227502B2 (en) | 2012-07-24 |
| NZ576781A (en) | 2012-02-24 |
| WO2008058679A3 (en) | 2008-07-10 |
| KR20090091166A (ko) | 2009-08-26 |
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